Method of inducing virus tolerance of plants

ABSTRACT

A method of inducing virus tolerance of plants which comprises treating the plants, the soil or seeds with an effective amount of a compound of the formula I  
                 
in which X is halogen, alkyl or trifluoromethyl; m is 0 or 1; 
     Q is C(═CH—CH 3 )—COOCH 3 , C(═CH—OCH 3 )—COOCH 3 , C(═N—OCH 3 )—CONHCH 3 , C(═N—OCH 3 )—COOCH 3 , N(—OCH 3 )—COOCH 3 , or a group Q1  
                 
wherein # denotes the bond to the phenyl ring;    A is —0—B, —CH 2 O—B, —OCH 2 —B, —CH 2 S—B, —CH═CH—B, —C═C—B, —CH 2 O—N═C(R 1 )—B, —CH 2 S—N═C(R 1 )—B, —CH 2 O—N═C(R 1 )—CH═CH—B, or —CH 2 O—N═C(R 1 )—C(R 2 )═N—R 3 , where B is phenyl, naphthyl, 5- or 6-membered hetaryl or 5- or 6-membered hetero-cyclyl, containing one to three N atoms and/or one O or S atom or one or two O and/or S atoms, the ring systems being unsubstituted or substituted as defined in the description; 
       R 1  is hydrogen, cyano, alkyl, haloalkyl, cycloalkyl, alkoxy, or alkylthio;    R 2  is phenyl, phenylcarbonyl, phenylsulfonyl, 5- or 6-membered hetaryl, 5- or 6-membered hetarylcarbonyl or 5- or 6-membered hetarylsulfonyl, the ring systems being unsubstituted or substituted by one to three radicals R B , C 1 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkyl-carbonyl, C 2 -C 10 -alkenylcarbonyl, C 3 -C 10 -alkenylcarbonyl, C 1 -C 10 alkyl-sulfonyl, or C(═NOR A )—R B , the hydrocarbon radicals of these groups being unsubstituted or substituted as defined in the description;    R 3  is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, the hydrocarbon radicals of these groups being unsubstituted or substituted as defined in the description; which is taken up by the plants or seeds, during the first six weeks of the growth period of the plants or germination of the seeds.

The present invention relates to a method of inducing virus tolerance ofplants which comprises treating the plants, the soil or seeds with aneffective amount of a compound of the formula I

in which

-   X is halogen, C₁-C₄-alkyl or trifluoromethyl;-   m is 0 or 1;-   Q is C(═CH—CH₃)—COOCH₃, C(═CH—OCH₃)—COOCH₃, C(═N—OCH₃)—CONHCH₃,    C(═N—OCH₃)—COOCH₃, N(—OCH₃)—COOCH_(3,) or a group Q1    -   wherein # denotes the bond to the phenyl ring;-   A is —O—B, —CH₂O—B, —OCH₂—B, —CH₂S—B, —CH═CH—B, —C═C—B,    —CH₂O—N═C(R¹)—B, —CH₂S—N═C(R¹)—B, —CH₂O—N═C(R¹)—CH═CH—B, or    —CH₂O—N═C(R¹)—C(R²)═N—R³,    -   where    -   B is phenyl, naphthyl, 5- or 6-membered hetaryl 5- or 6-membered        hetero-cyclyl, containing one to three N atoms and/or one O or S        atom or one or two O and/or S atoms, the ring systems being        unsubstituted or substituted by one to three radicals R^(a):        -   R^(a) is cyano, nitro, amino, aminocarbonyl,            aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,            C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulfonyl,            C₁-C₆-alkylsulfinyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,            C₁-C₆-haloalkoxy, C₁-C₆-alkyloxycarbonyl, C₁-C₆-alkylthio,            C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,            C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylamino-carbonyl,            C₁-C₆-alkylaminothiocarbonyl,            di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl,            C₂-C₆-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or            6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or            6-membered hetaryloxy, C(═NOR^(a))—R^(b) or            OC(R^(B))₂—C(R^(b))═NOR^(b), the cyclic radicals, in turn,            being unsubstituted or substituted by one to three radicals            R^(b):            -   R^(b) is cyano, nitro, halogen, amino, aminocarbonyl,                aminothiocarbonyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,                C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfinyl,                C₃-C₆-cycloalkyl, C-₁-alkoxy, C₁-C₆-haloalkoxy,                C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino,                di-C₁-C₆alkylamino, C₁-C₆-alkylaminocarbonyl,                di-C₁-C₆-alkylamino-carbonyl,                C₁-C₆-alkylaminothiocarbonyl,                di-C₁C₆alkylaminothiocarbonyl, C₂-C₆-alkenyl,                C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,                phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or                6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or                6-membered hetaryloxy or C(═NOR^(A))—R^(B);            -   R^(A), R^(B) are hydrogen or C₁-C₆-alkyl;    -   R¹ is hydrogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, or C₁-C₄-alkylthio;    -   R² is phenyl, phenylcarbonyl, phenylsulfonyl, 5- or 6-membered        hetaryl, 5- or 6-membered hetarylcarbonyl or 5- or 6-membered        hetarylsulfonyl, the ring systems being unsubstituted or        substituted by one to three radicals R^(a),    -    C₁-C₁₀-alkyl, C₃-C₆cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,        C₁-C₁₀alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl,        C₃-C₁₀-alkenylcarbonyl, C₁-C₁₀-alkylsulfonyl, or        C(═NOR^(A))—R^(B), the hydrocarbon radicals of these groups        being unsubstituted or substituted by one to three radicals        R^(c):        -   R^(c) is cyano, nitro, amino, aminocarbonyl,            aminothiocarbonyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,            C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfinyl, C₁-C₆-alkoxy,            C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio,            C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,            C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl,            C₁-C₆-alkylaminothiocarbonyl,            di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl,            C₂-C₆-alkenyloxy,        -    C₃-C₆-cycloalkyl, C₃C₆-cycloalkyloxy, 5- or 6-membered            heterocyclyl, 5- or 6-membered heterocyclyloxy, benzyl,            benzyloxy, phenyl, phenoxy, phenylthio, 5- or 6-membered            hetaryl, 5- or 6-membered hetaryloxy and hetarylthio, it            being possible for the cyclic groups, in turn, to be            partially or fully halogenated or to have attached to them            one to three radicals R^(a); and        -   R³ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl. C₂-C₆-alkynyl,            the hydrocarbon radicals of these groups being unsubstituted            or substituted by one to three radicals R^(c);            which is taken up by the plants or seeds, during the first            six weeks of the growth period of the plants or germination            of the seeds.

A large number of representatives of the highly heterogeneous group ofplant viruses (phytophages) are capable of attacking economicallyrelevant plants; the symptoms of the damage range from morphologicalmodifications to the death of the plants. The very many ways in whichviruses are transmitted (for example mechanically via wounding, viaseeds and pollen, or via vectors such as nematodes and insects), theproblems of diagnosis and the lack of suitable active ingredients makethe control of such viruses extraordinarily difficult; the emphasis istherefore on preventative and phytosanitary measures. Accordingly,preventing viral diseases in plants is an important aim in agriculture.

The search for methods for preventing viral diseases in plants hasalready yielded anti-viral active ingredients, some of which resemblenucleic acids. However, some of these substances generate mutants andinhibit the metabolism of nucleic adds and proteins in the host cells,giving rise to damage. In the field, these materials have only a smallactual control effect.

A sophisticated principle is the utilization, or stimulation, of theplants' intrinsic defenses:

DE-A 39 34 761 proposes polylysine and alkyldiethylene-triaminoaceticacids for preventing viral diseases of plants. EP-A 420 803 describesthe immunizing effect of benzo-1,2,3-thiazole derivatives againstvarious phytopathogenic microorganisms. WO-A 96/37493 discloses asimilar effect of pyridylthiazoles.

DD 280 030 proposes sulfonic acid derivatives as agents for activatingthe resistance of crop plants and useful plants. However, the action ofthese substances is unsatisfactory in many cases.

It is an object of the present invention to provide a method which canbe used broadly, which does not damage the plants and which brings abouteffective immunization of the plants against viral diseases.

We have found that this object is achieved by the method defined at theoutset. The active ingredients used are known as fungicides and, in somecases, also as insecticides (EP-A 178 826; EP-A 253 213; WO 93/15046; WO95/18789; WO 95/21153; WO 95/21154; WO 95/24396; WO 96/01256; WO97/15552; WO 97/27189). However, there has been no suggestion to datethat these active ingredients might have a stimulatory effect on theplants' intrinsic immune system against viruses.

The good compatibility, with plants, of the active ingredients of theformula I at the concentrations required for controlling plant diseasespermits the treatment of aerial plant parts and also the treatment ofpropagation material and seed, and of the soil.

In the method according to the invention, the active ingredients aretaken up by the plant either through the roots, finally causing overallprotection of the plant.

Thus, the protective action after carrying out the method according tothe invention is not just found in those plant parts, which have beensprayed directly, but the tolerance to viral diseases of the entireplant is increased.

In a preferred embodiment of the method, the aerial plant parts aretreated with a formulation of the active ingredient I.

The publications cited at the outset describe synthesis routes for thepreparation of the active ingredients used in the method according tothe invention, the disclosure of which is hereby incorporated.

Especially preferred for the method according to the invention areactive ingredients with the following meanings of the substituents, ineach case alone or in combination, the disclosure of the publicationscited being hereby incorporated:

Especially preferred for the method according to the invention are, ascomponent 1, the active ingredients of the formulae II to VIII, in which

-   V is OCH₃ and NHCH₃,-   Y is CH and N and-   T and Z independently of one another are CH and N.

Preferred active ingredients of the formula I in which Q isN(—OCH₃)—COOCH₃ are the compounds described in the publications WO93/15046 and WO 96/01256.

Preferred active ingredients of the formula I in which Q isC(═CH—OCH₃)—COOCH₃ are the compounds described in the publications EP-A178 826 and EP-A 278 595.

Preferred active ingredients of the formula I in which Q isC(═N—OCH₃)—COOCH₃ are the compounds described in the publications EP-A253 213 and EP-A 254 426.

Preferred active ingredients of the formula I in which Q isC(═N—OCH₃)—CONHCH₃ are the compounds described in the publications EP-A398 692, EP-A 477 631 and EP-A 628 540.

Preferred active ingredients of the formula I in which Q isC(═CH—CH₃)—COOCH₃ are the compounds described in the publications EP-A280 185 and EP-A 350 691.

Preferred active ingredients of the formula I in which Q is—CH₂O—N═C(R¹)—B are the compounds described in the publications EP-A 460575 and EP-A 463 488.

Preferred active ingredients of the formula I in which A is —O—B are thecompounds described in the publications EP-A 382 375 and EP-A 398 692.

Preferred active ingredients of the formula I in which A is—CH₂O—N═C(R¹)—C(R²)═N—OR³ are the compounds described in thepublications WO 95/18789, WO 95/21153, WO 95/21154, WO 97/05103 and WO97/06133.

Especially preferred are the active ingredients of the formula I inwhich

-   Q is N(—OCH₃)—COOCH₃,-   A is CH₂—O— and-   B is 3-pyrazolyl or 1,2,4-triazolyl, where B has attached to it one    or two substituents selected from the group of    -   halogen, methyl and trifluoromethyl and    -   phenyl and pyridyl, in particular 2-pyridyl, substituted by 1 to        3 radicals R^(b).

These active ingredients are described by formula II,

in which T is a carbon or a nitrogen atom, R^(a′) is halogen, methyl andtrifluoromethyl, y is zero, 1 or 2, R^(b) is as defined for formula I, xis zero, 1, 2, 3 or 4.

More preferred active ingredients are those of formula II′:

in which R^(b) is as defined for formula I.

With regard to their use, the compounds compiled in the tables, whichfollow, are especially preferred. TABLE I II

Position of the group No. T (R^(a′))_(y) phenyl-(R^(b))_(x) (R^(b))_(x)Reference I-1 N — 1 2,4-Cl₂ WO 96/01256 I-2 N — 1 4-Cl WO 96/01256 I-3CH — 1 2-Cl WO 96/01256 I-4 CH — 1 3-Cl WO 96/01256 I-5 CH — 1 4-Cl WO96/01256 I-6 CH — 1 4-CH₃ WO 96/01256 I-7 CH — 1 H WO 96/01256 I-8 CH —1 3-CH₃ WO 96/01256 I-9 CH 5-CH₃ 1 3-CF₃ WO 96/01256 I-10 CH 1-CH₃ 53-CF₃ WO 99/33812 I-11 CH 1-CH₃ 5 4-Cl WO 99/33812 I-12 CH 1-CH₃ 5 — WO99/33812

TABLE II III

No. V Y R^(a) Reference II-1 OCH₃ N 2-CH₃ EP-A 253 213 II-2 OCH₃ N2,5-(CH₃)₂ EP-A 253 213 II-3 NHCH₃ N 2,5-(CH₃)₂ EP-A 477 631 II-4 NHCH₃N 2-Cl EP-A 398 692 II-5 NHCH₃ N 2-CH₃ EP-A 398 692 II-6 NHCH₃ N 2-CH₃,4-OCF₃ EP-A 628 540 II-7 NHCH₃ N 2-Cl, 4-OCF₃ EP-A 628 540 II-8 NHCH₃ N2-CH₃, 4-OCH(CH₃)—C(CH₃)═NOCH₃ EP-A 11 18 609 II-9 NHCH₃ N 2-Cl,4-OCH(CH₃)—C(CH₃)═NOCH₃ EP-A 11 18 609 II-10 NHCH₃ N 2-CH₃,4-OCH(CH₃)—C(CH₂CH₃)═NOCH₃ EP-A 11 18 609 II-11 OCH₃ CH 2,5-(CH₃)₂ EP-A226 917

TABLE III IV

No. V Y T R^(a) Reference III-1 OCH₃ CH N 2-OCH₃, 4-CF₃ WO 96/16047III-2 OCH₃ CH N 2-OCH(CH₃)₂, 4-CF₃ WO 96/16047 III-3 OCH₃ CH CH 2-CF₃EP-A 278 595 III-4 OCH₃ CH CH 4-CF₃ EP-A 278 595 III-5 NHCH₃ N CH 2-ClEP-A 398 692 III-6 NHCH₃ N CH 2-CF₃ EP-A 398 692 III-7 NHCH₃ N CH 2-CF₃,4-Cl EP-A 398 692 III-8 NHCH₃ N CH 2-Cl, 4-CF₃ EP-A 398 692

TABLE IV V

No. V Y R¹ B Reference IV-1 OCH₃ CH CH₃ (3-CF₃)C₆H₄ EP-A 370 629 IV-2OCH₃ CH CH₃ (3,5-Cl₂)C₆H₃ EP-A 370 629 IV-3 NHCH₃ N CH₃ (3-CF₃)C₆H₄ WO92/13830 IV-4 NHCH₃ N CH₃ (3-OCF₃)C₆H₄ WO 92/13830 IV-5 OCH₃ N CH₃(3-OCF₃)C₆H₄ EP-A 460 575 IV-6 OCH₃ N CH₃ (3-CF₃)C₆H₄ EP-A 460 575 IV-7OCH₃ N CH₃ (3,4-Cl₂)C₆H₃ EP-A 460 575 IV-8 OCH₃ N CH₃ (3,5-Cl₂)C₆H₃ EP-A463 488 IV-9 OCH₃ CH CH₃ CH═CH-(4-Cl)C₆H₄ EP-A 936 213

TABLE V VI

No. V R¹ R² R³ Reference V-1 OCH₃ CH₃ CH₃ CH₃ WO 95/18789 V-2 OCH₃ CH₃CH(CH₃)₂ CH₃ WO 95/18789 V-3 OCH₃ CH₃ CH₂CH₃ CH₃ WO 95/18789 V-4 NHCH₃CH₃ CH₃ CH₃ WO 95/18789 V-5 NHCH₃ CH₃ 4-F-C₆H₄ CH₃ WO 95/18789 V-6 NHCH₃CH₃ 4-Cl-C₆H₄ CH₃ WO 95/18789 V-7 NHCH₃ CH₃ 2,4-C₆H₃ CH₃ WO 95/18789 V-8NHCH₃ Cl 4-F-C₆H₄ CH₃ WO 98/38857 V-9 NHCH₃ Cl 4-Cl-C₆H₄ CH₂CH₃ WO98/38857 V-10 NHCH₃ CH₃ CH₂C(═CH₂)CH₃ CH₃ WO 97/05103 V-11 NHCH₃ CH₃CH═C(CH₃)₂ CH₃ WO 97/05103 V-12 NHCH₃ CH₃ CH═C(CH₃)₂ CH₂CH₃ WO 97/05103V-13 NHCH₃ CH₃ CH═ CH₃ WO 97/05103 C(CH₃)CH₂CH₃ V-14 NHCH₃ CH₃O-CH(CH₃)₂ CH₃ WO 97/06133 V-15 NHCH₃ CH₃ O-CH₂CH(CH₃)₂ CH₃ WO 97/06133V-16 NHCH₃ CH₃ C(CH₃)═NOCH₃ CH₃ WO 97/15552

TABLE VI VII

No. V Y R^(a) Reference VI-1 NHCH₃ N H EP-A 398 692 VI-2 NHCH₃ N 3-CH₃EP-A 398 692 VI-3 NHCH₃ N 2-NO₂ EP-A 398 692 VI-4 NHCH₃ N 4-NO₂ EP-A 398692 VI-5 NHCH₃ N 4-Cl EP-A 398 692 VI-6 NHCH₃ N 4-Br EP-A 398 692

TABLE VII VIII

No. Q R^(a) Reference VII-1 C(═CH—OCH₃)COOCH₃ 5-O-(2-CN—C₆H₄) EP-A 382375 VII-2 C(═CH—OCH₃)COOCH₃ 5-O-(2-Cl—C₆H₄) EP-A 382 375 VII-3C(═CH—OCH₃)COOCH₃ 5-O-(2-CH₃—C₆H₄) EP-A 382 375 VII-4 C(═N—OCH₃)CONHCH₃5-O-(2-Cl—C₆H₄) GB-A 2253624 VII-5 C(═N—OCH₃)CONHCH₃ 5-O-(2,4-Cl₂—C₆H₃)GB-A 2253624 VII-6 C(═N—OCH₃)CONHCH₃₃ 5-O-(2-CH₃—C₆H₄) GB-A 2253624VII-7 C(═N—OCH₃)CONHCH₃ 5-O-(2-CH₃,3-Cl—C_(6H) ₃) GB-A 2253624 VII-8C(═N—OCH₃)CONHCH₃ 4-F, 5-O-(2-CH₃—C₆H₄) WO 98/21189 VII-9C(═N—OCH₃)CONHCH₃ 4-F, 5-O-(2-Cl—C₆H₄) WO 98/21189 VII-10C(═N—OCH₃)CONHCH₃ 4-F, 5-O-(2-CH₃,3-Cl—C₆H₃) WO 98/21189 VII-11 Q1 4-F,5-O-(2-Cl—C₆H₄) WO 97/27189 VII-12 Q1 4-F, 5-O-(2-CH₃,3-Cl—C₆H₃) WO97/27189 VII-13 Q1 4-F, 5-O-(2,4-Cl₂—C₆H₃) WO 97/27189

Especially preferred are, in particular, the active ingredients:Compound I-5 (pyraclostrobin), II-1 (kresoxim-methyl), II-3(dimoxystrobin), II-11 (ZJ 0712), III-3 (picoxystrobin), IV-6(trifloxystrobin), IV-9 (enestroburin), V-16 (orysastrobin). VI-1(metominostrobin), VII-1 (azoxystrobin), and VII-11 (fluoxastrobin).

The compounds I increase the tolerance of plants to viruses. They areespecially important for controlling viruses on diverse crop plants suchas tobacco, barley, cucumber, potatoes and beet, and on the seeds ofthese plants.

The inventive method is useful to induce tolerance in plants againstviruses of various families, such as Avsunviroidae, Bromoviridae,Closteroviiidae, Fosxivinda, Geminiviridae, Luteoviridae, Nanoviridae,Parititiviridae, Pospiviroidae, Potyviridae, Reoviridae, dae,Mononegavirales, Rhabdoviridae, Sequiviridae, Tombusviridae, andTymoviridae.

It is particularly suitable to control the following genus: Benyvirus,Ilarvirus, Cucumovirus, Oleavirus, Tospovirus, Caulimovirus, Soymovirus,Cavemovirus, Peluvirus, Closterovirus, Comovirus; Crinivirus,Ampelovirus, Fabavirus, Nepovirus, Allexivirus, Manadrivirus,Carlavirus, Capillovirus, Foveavirus, Potexvirus, Trichovirus,Vitivirus, Furovirus, Mastrevirus, Curtovirus, Begomovirus, Hordeivirus,Idaeovirus, Luteovirus, Polervirus, Eanmovirus, Nanovirus, Ophiovirus,Ourmiavirus, Alphacryptovirus, Betacryptovirus, Pecluvirus, Pomovirus,Potyvirus, Rymovirus Bymovirus, Macluravirus, Ipomovirus, Tritimovirus,Fijivirus, Phytoreovirus, Oryzavirus, Cytorhabdovirus,Nucleorhabdovirus. Sequivirus, Waikavirus, Sobemovirus, Tenuivirus,Tobamovirus, Tobravirus, Tombusvirus, Carmovirus, Necrovirus,Dianthovirus, Machlomovirus, Avenavirus, Tymovirus, Marafivirus,Maculavirus, Umbravirus, Varicosavirus, Pospiviroid, Hostuviroid,Cocadviroid, Apscaviroid, Coleviroid, Avsuniviroid, and Pelamoviroid.

More particularly, the inventive method is useful for controlling thefollowing species: Tobacco streak virus, Cucumber mosaic virus, Tomatospotted wilt virus, Soybean chlorotic mottle virus, Broad bean wiltvirus 1, Tobacco ringspot virus, Potato virus X, Soil-borne wheat mosaicvirus, Barley stripe mosaic virus, Potato leafroll virus, Ourmia melonvirus, Peanut clump virus, Potato mop-top virus, Potato virus Y, Barleyyellow mosaic virus, Wheat streak mosaic virus, Potato yellow dwarfvirus, Tobacco necrosis virus satellite, Southern bean mosaic virus,Tobacco mosaic virus, Tobacco rattle virus, Tomato bushy stunt virus,Tobacco necrosis virus A, Maize chlorotic mottle virus, Maize rayadofino virus, and Potato spindle tuber viroid.

Specifically, they are suitable for controlling the following plantdiseases:

-   -   in tobacco, the tobacco mosaic virus and the tobacco necrosis        virus,    -   in beans, the bean common mosaic virus and the bean yellow        mosaic virus,    -   in barley, the barley stripe mosaic virus and the barley yellow        dwarf virus (DYDV),    -   in cucumbers, the cucumber green mottle mosaic virus and the        cucumber mosaic virus,    -   in potatoes, the potato X virus and the potato y virus,    -   in beet, rhizomnania and beet mild yellowing virus.

The application of the compound I preferably is made during the firstsix weeks, preferably four weeks of the growth period of the plants,long before first protective application against fungi usually is made.

The plant is treated before infection takes place, preferably severalweeks to one week before the expected virus attack. During suchtimeframe one to 10 applications are carried out. A markedly reducedsusceptibility of the plant to viral diseases is observed.

In case of vegetables and field crops the active ingredients arepreferably applied shortly after germination of the plants, especiallywithin the first four weeks after germination. In case of fruits andother perennial plants the first application is made before begin orwithin the first four weeks of the growth period. In all cases bestefficacy is observed, when the application is repeated every 10 to 20days.

The method according to the invention is preferably carried out asfoliar application when applied to fruit and vegetables, such aspotatoes, tomatoes, cucurbits, preferably cucumbers, melons,watermelons, garlic, onions, and lettuce. Preferably more than twoapplications, and up to 10 applications during a season are carried out.

The method according to the invention is preferably carried out asfoliar application when applied to fruits, such as apples, stone fruits,and citrus. Preferably more than two applications, and up to 5applications during a season are carried out.

The method of the invention can also be applied to field crops, such assoybeans, corn, cotton, tobacco, common beans, wheat, barley, peas, andothers. In relation to these crops the method is preferably applied bytreating the seeds or the plants. The plants are preferably treated withtwo to three applications.

For use in crop protection, the application rates are between 0.01 and2.0 kg, preferably up to 1.0 kg of active ingredient per hectare,depending on the type of pathogen and the plant species.

In the treatment of seed, amounts of from 0.001 to 0.1 g, preferably0.01 to 0.05 g, of active ingredient are generally required per kilogramof seed.

The compounds I can be converted into the formulations conventionallyused for fungicides, for example solutions, emulsions, suspensions,dusts, powders, pastes and granules. The use form depends on theparticular purpose; in any case, it should ensure fine and uniformdistribution of the compound according to the invention.

Best results are obtained when a formulation is used which supports thetransport of the active compounds into the plants, and the distributionwithin the entire plant in the sap.

The formulations are prepared in a known manner (see e.g. for reviewU.S. Pat. No. 3,060,084. EP-A 707 445 (for liquid concentrates),Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48,Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York,1963, pages 8-57 and et seq. WO 91/13546, U.S. Pat. No. 4,172,714, U.S.Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, U.S. Pat. No. 5,180,587,U.S. Pat. No. 5,232,701, U.S. Pat. No. 5,208,030, GB 2,095,558, U.S.Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley andSons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H.,Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim(Germany), 2001, 2. D. A. Knowles, Chemistry and Technology ofAgrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998(ISBN 0-7514-0443-8), for example by extending the active compound withauxiliaries suitable for the formulation of agrochemicals, such assolvents and/or carriers, if desired emulsifiers, surfactants anddispersants, preservatives, anti-foaming agents, anti-freezing agents.

Examples of suitable solvents are water, aromatic solvents (for exampleSolvesso products, xylene), paraffins (for example mineral oilfractions), alcohols (for example methanol, butanol, pentanol, benzylalcohol), ketones (for example cyclohexanone, gamma-butyrolactone),pyrrolidones (NMP. NOP), acetates (glycol diacetate), glycols, fattyacid dimethylamides, fatty acids and fatty acid esters. In principle,solvent mixtures may also be used.

Suitable emulsifiers are nonionic and anionic emulsifiers (for examplepolyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates).

Examples of dispersants are lignin-sulfite waste liquors andmethylcellulose.

Suitable surfactants used are alkali metal, alkaline earth metal andammonium salts of lignosulfonic acid, naphthalenesulfonic acid,phenolsulfonic acid, dibutylnaphthalene-sulfonic acid,alkylarylsufonates, alkyl sulfates, alkylsulfonates, fatty alcoholsulfates, fatty acids and sulfated fatty alcohol glycol ethers,furthermore condensates of sulfonated naphthalene and naphthalenederivatives with formaldehyde, condensates of naphthalene or ofnaphthalenesulfonic acid with phenol and formaldehyde, polyoxy-ethyleneoctylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol,alkyl-phenol polyglycol ethers, tributylphenyl polyglycol ether,tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcoholand fatty alcohol ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, laurylalcohol polyglycol ether acetal, sorbitol esters, lignosulfate wasteliquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayablesolutions, emulsions, pastes or oil dispersions are mineral oilfractions of medium to high boiling point, such as kerosene or dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, for example toluene,xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or theirderivatives, methanol, ethanol, propanol, butanol, cyclohexanol,cyclohexanone, isophorone, highly polar solvents, for example dimethylsulfoxide, N-methylpyrrolidone or water.

Also anti-freezing agents such as glycerin, ethylene glycol, propyleneglycol and bactericides such as can be added to the formulation.

Suitable antifoaming agents are for example antifoaming agents based onsilicon or magnesium stearate.

Suitable preservatives are for example Dichlorophenyl andenzylalkoholhemiformal.

Seed Treatment formulations may additionally comprise binders andoptionally colorants.

Binders can be added to improve the adhesion of the active materials onthe seeds after treatment. Suitable binders are block copolymers EO/POsurfactants but also polyvinylalcohols, polyvinylpyrrolidones,polyacrylates, polymethacrylates, polybutenes, polyisobutylenes,polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines(Lupasol®, Polymin®), polyethers, polyurethans, polyvinylacetate, tyloseand copolymers derived from these polymers.

Powders, materials for spreading and dustable products can be preparedby mixing or concomitantly grinding the active substances with a solidcarrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active compounds tosolid carriers.

Examples of solid carriers are mineral earths such as silica gels,silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers, such as, forexample, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas,and products of vegetable origin, such as cereal meal, tree bark meal,wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active compound(s). In thiscase, the active compound(s) are employed in a purity of from 90% to100% by weight, preferably 95% to 100% by weight (according to NMRspectrum).

For seed treatment purposes, respective formulations can be diluted 2-10fold leading to concentrations in the ready to use preparations of 0.01to 60% by weight active compound by weight, preferably 0.1 to 40% byweight.

The compounds I can be used as such, in the form of their formulationsor the use forms prepared therefrom, for example in the form of directlysprayable solutions, powders, suspensions or dispersions, emulsions, oildispersions, pastes, dustable products, materials for spreading, orgranules, by means of spraying, atomizing, dusting, spreading orpouring. The use forms depend entirely on the intended purposes; theyare intended to ensure in each case the finest possible distribution ofthe active compound(s) according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (sprayable powders, oil dispersions) by adding water.To prepare emulsions, pastes or oil dispersions, the substances, as suchor dissolved in an oil or solvent, can be homogenized in water by meansof a wetter, tackifier, dispersant or emulsifier. However, it is alsopossible to prepare concentrates composed of active substance, wetter,tackifier, dispersant or emulsifier and, if appropriate, solvent or oil,and such concentrates are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations canbe varied within relatively wide ranges. In general, they are from0.0001 to 10%, preferably from 0.01 to 1% per weight

The active compound may also be used successfully in theultra-low-volume process (ULV), it being possible to apply formulationscomprising over 95% by weight of active compound, or even to apply theactive compound without additives.

The following are examples of formulations: 1. Products for dilutionwith water for foliar applications. For seed treatment purposes, suchproducts may be applied to the seed diluted or undiluted.

A) Water-Soluble Concentrates (SL, LS)

10 parts by weight of the active compound(s) are dissolved in 90 partsby weight of water or a water-soluble solvent. As an alternative,wetters or other auxiliaries are added. The active compound(s) dissolvesupon dilution with water, whereby a formulation with 10% (w/w) of activecompound(s) is obtained.

B) Dispersible Concentrates (DC)

20 parts by weight of the active compound(s) are dissolved in 70 partsby weight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvinylpyrrolidone. Dilution with water givesa dispersion, whereby a formulation with 20% (w/w) of active compound(s)is obtained.

C) Emulsifiable Concentrates (EC)

15 parts by weight of the active compound(s) are dissolved in 7 parts byweight of xylene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). Dilution withwater gives an emulsion, whereby a formulation with 15% (w/w) of activecompound(s) is obtained.

D) Emulsions (EW, EO, ES)

25 parts by weight of the active compound(s) are dissolved in 35 partsby weight of xylene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). This mixture isintroduced into 30 parts by weight of water by means of an emulsifiermachine (e.g. Ultraturrax) and made into a homogeneous emulsion.Dilution with water gives an emulsion, whereby a formulation with 25%(w/w) of active compound(s) is obtained.

E) Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compound(s)are comminuted with addition of 10 parts by weight of dispersants,wetters and 70 parts by weight of water or of an organic solvent to givea fine active compound(s) suspension. Dilution with water gives a stablesuspension of the active compound(s), whereby a formulation with 20%(w/w) of active compound(s) is obtained.

F) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50 parts by weight of the active compound(s) are ground finely withaddition of 50 parts by weight of dispersants and wetters and made aswater-dispersible or water-soluble granules by means of technicalappliances (for example extrusion, spray tower, fluidized bed). Dilutionwith water gives a stable dispersion or solution of the activecompound(s), whereby a formulation with 50% (w/w) of active compound(s)is obtained.

G) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS, WS)

75 parts by weight of the active compound(s) are ground in arotor-stator mill with addition of 25 parts by weight of dispersants,wetters and silica gel. Dilution with water gives a stable dispersion orsolution of the active compound(s), whereby a formulation with 75% (w/w)of active compound(s) is obtained.

2. Products to be applied undiluted for foliar applications. For seedtreatment purposes, such products may be applied to the seed diluted.

I) Dustable Powders (DP, DS)

5 parts by weight of the active compound(s) are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dustable product having 5% (w/w) of active compound(s)

J) Granules (GR, FG, GG, MG)

0.5 part by weight of the active compound(s) is ground finely andassociated with 95.5 parts by weight of carriers, whereby a formulationwith 0.5% (w/w) of active compound(s) is obtained. Current methods areextrusion, spray-drying or the fluidized bed. This gives granules to beapplied undiluted for foliar use.

K) ULV Solutions (UL)

10 parts by weight of the active compound(s) are dissolved in 90 partsby weight of an organic solvent, for example xylene. This gives aproduct having 10% (w/w) of active compound(s), which is appliedundiluted for foliar use.

Conventional seed treatment formulations include for example flowableconcentrates FS, solutions LS, powders for dry treatment DS, waterdispersible powders for slurry treatment WS, water-soluble powders SSand emulsion ES and EC and gel formulation GF. These formulation can beapplied to the seed diluted or undiluted. Application to the seeds iscarried out before sowing, either directly on the seeds.

In a preferred embodiment a FS formulation is used for seed treatment.Typically, a FS formulation may comprise 1-800 g/l of active ingredient,1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l ofbinder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent,preferably water.

The note mentioning the effect of the active ingredients I in inducingresistance to viruses may be present as a label on the packaging or inproduct data sheets. The note may also be present in the case ofpreparations which can be used in combination with the activeingredients I.

The induction of resistance may also constitute an indication which maybe the subject of official approval of the active ingredients I.

The action of the compounds of the general formula I was demonstrated bythe following experiments:

Use examples for induction of resistance to viruses

Plant Material

For the experiments, tobacco plants (Nicotinia tabacum cv. Xanthi-nc)were grown at 25° C., an atmospheric humidity of 59% and a dailyphotoperiod of 16 hours (150-200 μM quanta/s⁻¹/m⁻²) for 4 to 5 weeks inpotting compost (standard soil type ED 73). Some of the plants were fedonce per week by adding a commercial house-plant fertilizer (10% totalnitrogen, 9% phosphate, 7% potash) to the irrigation water at therecommended rate.

Application of the Active Ingredient

The formulated active ingredient used took the form of water-dispersiblegranules with an active ingredient content of 20%. The concentrationsused in the experiments (0.01-10 mM) are based on the active ingredientcontent. To prevent distribution of the active ingredient in the entireplant, the stalks of plants where a leaf had been infiltrated wereremoved above the treated leaf, using a sterile surgical blade.

After the application of the active ingredient, and also after infectionwith the virus at a later time, the plants were left to stand in thegrowth cabinet.

Virus infection and resistance assessment (following Malamy et al.,SCIENCE Vol. 250, pp. 1002-1004 (1990)):

The various pretreated tobacco plants were infected with tobacco mosaicvirus (TMV, strain U1). To this end, a viral stock solution was dilutedwith 50 mM phosphate buffer (pH 7) to a final concentration of 1 μg TMVcoat protein/ml. Infection was carried out by gently rubbing leaves,whose surfaces had previously been sprinkled with silicon carbide, witha gauze bandage soaked in the TMV solution. Post-infection, the siliconcarbide was rinsed from the leaves with a gentle water jet and theplants were left to stand under the above-described conditions.Infection with TMV was carried out 1 day after the pretreatment. Five to7 days post-infection, the diameter of 10 to 20 lesions on the leaveswas determined.

The lesion diameter is a measure of the acquired resistance of theplants, the smallest lesions representing the highest acquiredresistance.

USE EXAMPLE 1

Individual leaves of the plants were perforated at several sites with acannula, and the aqueous active ingredient solution was injected intothe leaf at the perforation sites using a syringe (rate of application 2to 5 ml/leaf). The insoluble components of the solution of the activeingredient had previously been removed either by sedimentation or bybrief spinning (3 minutes at 5,000 g). In case of the control plants,the leaves were injected with water.

After 7 days, the diameter of the lesions on the leaves caused by TMVwas determined in millimeters [mm].

In this test, the plants treated with 1 mM of the active ingredient I-5in Table I showed lesions averaging 2.35 mm and the plants treated with2.5 mM showed 1.8 mm, while the plants treated with pure water ascontrol showed lesions of 3.55 mm.

USE EXAMPLE 2

One half of the treated leaf was infiltrated with the active ingredientsolution (preparation as in Example 1), while the other half wasinfiltrated with water. This procedure was intended to excludevariations in the response between different leaves and to make possiblea direct determination on the effect of the active ingredient.

After 5 days, the diameter of the lesions on the leaves caused by TMVwas determined in millimeters [mm].

In this test the leaf zones treated with 0.5 and 1 mM of the activeingredient I-5 in Table I showed lesions averaging 2.75 and 2.85 mm,respectively, and the untreated leaf zones showed lesions of 4.15 and4.25 mm, while the plants treated with pure water as control showedlesions of 3.2 and 3.35 mm.

USE EXAMPLE 3

Leaf halves of approx. 5-weeks-old tobacco plants (cultivar Xanthi-nc)were infiltrated with 1 mM active ingredient solution in 1% aqueousethanol; the leaf halves of the controls were infiltrated with 1%aqueous ethanol.

Infection with TMV was carried our 1 day after treatment; the plantswere evaluated after further 5 days. The data shown are the averages ofthe leaf areas which had died owing to viral attack (lesions) at theinfection site on leaf halves treated with active ingredient oruntreated leaf halves (controls):

Area of the lesions in comparison with the control: Active ingredientArea in percent I-5 53.0 II-3 68.1 III-4 60.3 IV-3 76.1 V-16 63.8 VII-162.1

USE EXAMPLE 4

The procedure of use example 3 was followed, but infection was carriedout 2 days after the treatment and the plants were evaluated afterfurther 5 days.

Area of the lesions in comparison with the control: Active IngredientArea In percent II-3 62.7 III-4 78.4 VII-1 70.4

USE EXAMPLE 5

Spraying the Leaves with Active Ingredient Solutions

In each case 2 mM active ingredient were dissolved in water with the aidof a universal wetter in the ratio 1:1 (w/w) and sprayed onto the leafhalves of 5-week-old tobacco plants (cultivar Xanthi-nc) (leaf halves ofthe controls were sprayed with dissolved wetter only).

Infection with TMV was carried out 5 days after the treatment, and theplants were evaluated after further 4 days. The data shown are theaverages of the leaf areas which had died owing to viral attack(lesions) at the infection site on leaf halves treated with activeingredient or untreated leaf halves (controls):

Area of the lesions in comparison with the control: Active ingredientArea in percent II-3 49.6 III-4 73.6 VII-1 68.3

USE EXAMPLE 6

Enhanced Plant Growth and Tolerance to Viral Infection FollowingTreatments

The experiments were performed in greenhouse of under appropriategrowing conditions for tomatoes. Tomato plants (cultivar Gaucho) weregrown in pots until development of the first two true leaves. Then theplantlets were sprayed with different concentrations of formulatedPyraclostrobin (compound I-5; commercial fungicide Cabrio Top® of BASFAktiengesellschaft). These treatments were done either 120 hours beforeor following inoculation of the plantlets with TMV, representingprotective and curative situation. The treatments were run with 5replicates, each containing 3 plantlets. 30 days after last treatmentthe plants were analyzed for visual plant growth (altitude and dry mass)and chlorophyll content (photometric measurement of extracts). Also thevirus titre was determined (ELISA). Chlorophyll Dry weight Altidude No.Treatment [μg fresh weight] [g] [cm] 1 Non infected control 12.5 bc 1.54a 25.59 a 2 TMV infected, untreated 10.8 bc 0.30 ef 9.53 f 3 Cabrio Top1.5 g/L⁻¹ Preventive 18.6 a 0.74 b 18.3B bc 4 Cabrio Top 1.5 g/L⁻¹Curative 11.5 bc 0.35 ef 12.48 def

Same letters indicate non significant differences (Tukey; P≦0.05).

As shown by the data, protective treatment of plants with Pyraclostrobincan prevent growth inhibition and loss of leaf chlorophyll caused by TMVinfection. Curative treatment showed no advantage compared withuntreated plants.

1. A method of inducing virus tolerance of plants which comprisestreating the plants, the soil or seeds, with an effective amount of acompound of the formula I

in which X is halogen, C₁-C₄-alkyl or trifluoromethyl; m is 0 or 1; Q isC(═CH—CH₃)—COOCH₃, C(═CH—OCH₃)—COOCH₃, C(═N—OCH₃)—CONHCH₃,C(═N—OCH₃)—COOCH₃, N(—OCH₃)—COOCH₃, or a group Q1

wherein # denotes the bond to the phenyl ring; A is —O—B, —CH₂O—B,—OCH₂—B, —CH₂S—B, —CH═CH—B, —C≡C—B, —CH₂O—N═C(R¹)—B, —CH₂S—N═C(R¹)—B,—CH₂O—N═C(R¹)—CH═CH—B, or —CH₂O—N═C(R¹)—C(R²)═N—OR³, where B is phenyl,naphthyl, 5-membered or 6-membered hetaryl or 5-membered or 6-memberedheterocyclyl, containing one to three N atoms and/or one O or S atom orone or two O and/or S atoms, the ring systems being unsubstituted orsubstituted by one to three radicals R^(a): R^(a) is cyano, nitro,amino, aminocarbonyl, aminothiocarbonyl, halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylsulfonyl,C₁-C₆-alkylsulfinyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkyloxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino,di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl,di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl,di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy,phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or6-membered hetaryl, 5- or 6-membered hetaryloxy, C(═NOR^(a))—R^(b) orOC(R^(a))₂—C(R^(b))═NOR^(b), the cyclic radicals, in turn, beingunsubstituted or substituted by one to three radicals R^(b): R^(b) iscyano, nitro, halogen, amino, aminocarbonyl, aminothiocarbonyl,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfinyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl,C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl,C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkyl-aminothiocarbonyl,C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-memberedheterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy orC(═NOR^(A))—R^(B); R^(A), R^(B) are hydrogen or C₁-C₆-alkyl; R¹ ishydrogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy, or C₁-C₄-alkylthio; R² is phenyl, phenylcarbonyl,phenylsulfonyl, 5- or 6-membered hetaryl, 5- or 6-memberedhetarylcarbonyl or 5- or 6-membered hetarylsulfonyl, the ring systemsbeing unsubstituted or substituted by one to three radicals R^(a),C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₁-C₁₀-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₃-C₁₀-alkenylcarbonyl,C₁-C₁₀-alkylsulfonyl, or C(═NOR^(a))—R^(b), the hydrocarbon radicals ofthese groups being unsubstituted or substituted by one to three radicalsR^(c): R^(c) is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl,halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl,C₁-C₆-alkylsulfinyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino,di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl,di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl,di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy. 5- or 6-membered heterocyclyl, 5-or 6-membered heterocyclyloxy, benzyl, benzyloxy, phenyl, phenoxy,phenylthio, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy andhetarylthio, it being possible for the cyclic groups, in turn, to bepartially or fully halogenated or to have attached to them one to threeradicals R^(a); and R³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkenyl,C₂-C₆-alkynyl, the hydrocarbon radicals of these groups beingunsubstituted or substituted by one to three radicals R^(c); which istaken up by the plants or seeds, during the first six weeks of thegrowth period of the plants, or germination of the seeds.
 2. A method asclaimed in claim 1, wherein in formula I the index m is zero and thesubstituents have the following meanings: Q is C(═CH—CH₃)—COOCH₃,C(═CH—OCH₃)—COOCH₃, C(═N—OCH₃)—CONHCH₃, C(═N—OCH₃)—COOCH₃, orN(—OCH₃)—COOCH₃; A is —O—B, —CH₂O—B, —OCH₂—B, —CH₂O—N═C(R¹)—B, or—CH₂O—N═C(R¹)—C(R²)═N—OR³, where B is phenyl, pyridyl, pyrimidyl,pyrazolyl, triazolyl, these ring systems being unsubstituted orsubstituted by one to three radicals R^(a); R¹ is hydrogen, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, or C₁-C₄-alkoxy; R² isC₁-C₆-alkyl, C₂C₁₀-alkenyl, C₃-C₆-cycloalkyl, these groups beingunsubstituted or substituted by one or two radicals R^(b′); R^(b′) isC₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, benzyl,phenyl, or phenoxy; phenyl, which is unsubstituted or substituted by oneor two radicals R^(a); and R³ is C₁-C₆-alkyl, C₂-C₆-alkenyl, orC₂C₆-alkynyl
 3. A method as claimed in claim 1, wherein an activeingredient of formula II

in which T is a carbon or a nitrogen atom, R^(a′) is halogen, methyl andtrifluoromethyl. y is zero, 1 or 2, R^(b) is as defined for formula I, xis zero, 1, 2, 3 or 4 is used.
 4. A method as claimed in claim 1,wherein an active ingredient of formula III

in which T is a carbon or a nitrogen atom, R^(a) represents one or twoidentical or different groups selected from halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, halogenmethyl, halogenmethoxy, methyl and trifluoromethyl,which R^(a) groups are unsunstituted or substituted by aC₁-C₆-alkoxyimino group; V is OCH₃, or NHCH₃; and Y is CH or N; is used.5. A method as claimed in claim 1, wherein compound I is selected from:pyraclostrobin, kresoxim-methyl, dimoxystrobin,2-(ortho((2,5-Dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylic acidmethyl ester, picoxystrobin, trifloxstrobin, enestroburin, orysastrobin,metominostrobin, azoxystrobin, and fluoxastrobin.
 6. A method as claimedin claim 1, wherein compound I is selected from: pyraclostrobin,kresoxim-methyl, dimoxystrobin,2-(ortho-((2,6-Dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylicacid methyl ester, picoxystrobin, trifoxystrobin, enestroburin,orysastrobin, metominostrobin, azoxystrobin, and fluoxastrobin.
 7. Amethod as claimed in claim 1, wherein compound I is selected from:azoxystrobin, pyraclostrobin, and picoxystrobin.
 8. A method as claimedin claim 1 wherein application is made during the first four weeks ofthe growth period of the plants or germination of the seeds.
 9. A methodas claimed in claim 1 wherein repeated applications of a compound I aremade.
 10. A method as claimed in claim 1 wherein repeated application ofa compound I is made every 10 to 20 days.
 11. A method as claimed inclaim 1 wherein two to ten applications of a compound I during a seasonare made.
 12. A method as claimed in claim 1 which is carried out asfoliar application.
 13. A method as claimed in claim 1 applied tovegetables and field crops wherein application is carried out shortlyafter germination of the plants.
 14. A method as claimed in claim 13wherein application is carried out within the first four weeks aftergermination.
 15. A method as claimed in claim 1 applied to of fruit andvegetables which comprises more than two, and up to ten applications ofa compound I.
 16. A method as claimed in claim 1 applied to of fruitsand other perennial plants wherein the first application is made beforebegin of the growth period.
 17. A method as claimed in claim 16 whereinthe first application is made within the first four weeks of the growthperiod.
 18. A method as claimed in claim 11 which is applied topotatoes, tomatoes, cucurbits, cucumbers, melons, watermelons, garlic,onions, and lettuce.
 19. A method as claimed in claim 11 which isapplied to apples, stone fruits, or citrus.
 20. A method as claimed inclaim 11 which is applied to soybeans, corn, cotton, tobacco, commonbeans, wheat, barley, and peas.